Polyol-based compounds

Abstract

The present invention relates to a polyol-based compound represented by the following chemical formula 1. [Chemical formula 1] (R, R1 and R2R are as defined in claim 1.)

Description

polyol compounds

[0001] According to embodiments of the present invention, it relates to a polyol compound.

[0002] Polyurethane and polyurethane-urea are used in a variety of fields, most notably as elastic fibers. In particular, fibers with a polyurethane-urea structure utilize polyether polyol as the soft segment component and a highly cohesive polyamine compound as the hard segment component, resulting in excellent elasticity and stretch recovery.

[0003] The main soft segment of polyurethane resins produced on an industrial scale, i.e., polyols, can be classified into polyether types represented by polypropylene glycol and polytetramethylene glycol, polyester polyol types represented by dicarboxylic acid polyesters, polylactone types represented by polycaprolactone, and polycarbonate types obtained by reacting a carbonate source with a diol.

[0004] However, with very few exceptions, most of these polyols are derived from petroleum. Considering global warming and environmental concerns, it's necessary to utilize biomass resources, such as plants, rather than petroleum-derived raw materials. Currently, the most widely used polyester polyol is synthesized from adipic acid. However, the nitric acid oxidation process used to manufacture adipic acid creates N2O, a greenhouse gas with a significantly greater global warming effect than CO2, posing a problem.

[0005] The present invention can provide a novel polyol compound and its use prepared from a naturally derived fatty acid or waste oil (e.g., used natural oil) in an environmentally friendly manner.

[0006] However, the problems to be solved by the present invention are not limited to those mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

[0007] According to one embodiment, the polyol compound may be a polyol compound represented by the following chemical formula 1.

[0008] [Chemical Formula 1]

[0009]

[0010] (In the above chemical formula 1, R is a substituent derived from an alkane or alkene or a fatty acid or fatty acid ester having a hydrocarbon group of 4 to 28 carbon atoms, or

[0011] R is, R3-NH- (R3 is a polyurethane-derived substituent, containing one or more moieties and -OH groups), or (R4 is a substituent derived from polyethylene terephthalate, moiety and one or more -OH groups.)

[0012] R1 is -(CH2)n-, -(CH2)nO-(CH2)n- or -(CH2)n-CH(OH)-(CH2)n- (n is an integer from 1 to 10),

[0013] R2 may be selected from hydrogen, a monoglyceride-derived substituent, a diglyceride-derived substituent, a triglyceride-derived substituent, an A substituent having 1 to 10 carbon atoms and composed of hydrogen and oxygen, or an A-1 substituent having 1 to 10 carbon atoms, composed of hydrogen and oxygen, and including at least one ether bond (-OC-) in the molecule (provided that the A substituent and the A-1 substituent do not include an "-OH" group).

[0014] According to one embodiment, the composition of the present invention may be a composition comprising one or more or two or more of the polyol compounds represented by the chemical formula 1 disclosed in the present invention.

[0015] According to one embodiment, the present invention can provide a novel bio-polyol compound and its use.

[0016] According to one embodiment, the present invention can provide a novel bio-polyol compound prepared from naturally occurring fatty acids or waste oils (e.g., used natural oils).

[0017] According to one embodiment, the present invention can provide a novel polyol-based compound constituting a polyol segment of polyurethane.

[0018] According to one embodiment, the present invention can provide a precursor composition for polyurethane comprising a novel polyol-based compound according to the present invention. For example, the precursor composition can be applied to the production of polyurethane produced by reaction with an isocyanate.

[0019] Hereinafter, embodiments of the present invention will be described in detail. In describing the present invention, detailed descriptions of related, known functions or configurations will be omitted if they are deemed to unnecessarily obscure the gist of the present invention. Furthermore, the terms used in this specification are intended to appropriately express preferred embodiments of the present invention and may vary depending on the intent of the user or operator, or on customary practices in the field to which the present invention pertains. Therefore, definitions of these terms should be based on the overall content of this specification.

[0020] Throughout the specification, when we say that an element is "on" another element, this includes not only cases where the element is in contact with the other element, but also cases where another element exists between the two elements.

[0021] Throughout the specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components.

[0022] In this document, phrases such as "A or B", "at least one of A and B", "at least one of A or B", "A, B, or C", "at least one of A, B, and C", and "at least one of A, B, or C" can each include any one of the items listed together with the corresponding phrase, or all possible combinations thereof. Terms such as "first", "second", or "first" or "second" may be used merely to distinguish the corresponding element from other corresponding elements and do not limit the corresponding elements in any other respect (e.g., importance or order). For example, suitable results may be achieved even if the described techniques are performed in a different order than the described method, and / or the described elements are combined or combined in a different form than the described method, or are replaced or substituted by other elements or equivalents. Therefore, other implementations, other embodiments, and equivalents of the claims are also within the scope of the following claims.

[0023] Hereinafter, the polyol compound of the present disclosure will be described in detail with reference to examples. However, the present invention is not limited to these examples.

[0024] According to one embodiment, the polyol compound of the present invention may be a polyol compound represented by the following chemical formula 1.

[0025] [Chemical Formula 1]

[0026]

[0027] In one embodiment, in the above formula 1, R is a substituent derived from an alkane or alkene or a fatty acid or fatty acid ester having a hydrocarbon group of 4 to 28 carbon atoms, or

[0028] R is, R3-NH- (R3 is a polyurethane-derived substituent, containing one or more moieties and -OH groups), or (R4 is a substituent derived from polyethylene terephthalate, moiety and one or more -OH groups.)

[0029] R1 is -(CH2)n-, -(CH2)nO-(CH2)n- or -(CH2)n-CH(OH)-(CH2)n- (n is an integer from 1 to 10),

[0030] R2 may be selected from hydrogen, a monoglyceride-derived substituent, a diglyceride-derived substituent, a triglyceride-derived substituent, an A substituent having 1 to 10 carbon atoms and composed of hydrogen and oxygen, or an A-1 substituent having 1 to 10 carbon atoms, composed of hydrogen and oxygen, and including at least one ether bond (-OC-) in the molecule (provided that the A substituent and the A-1 substituent do not include an "-OH" group).

[0031] For example, the hydrocarbon group may have 4 to 28 carbon atoms; 8 to 22 carbon atoms; 10 to 22 carbon atoms; 12 to 22 carbon atoms; 16 to 22 carbon atoms; 4 to 20 carbon atoms; 4 to 18 carbon atoms; 4 to 14 carbon atoms; or 4 to 12 carbon atoms; or 4 to 10 carbon atoms. For example, the hydrocarbon group may be a saturated or unsaturated hydrocarbon group (e.g., an unsaturated fatty acid).

[0032] In one embodiment, the fatty acid is caprylic acid, capric acid, lauric acid, myristic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, pentadecanoic acid, palmitic acid, arachidonic acid, myristoleic acid, palmitoleic acid, sapienic acid, elaidic acid, vaccenic acid; It can be oleic acid (a monounsaturated omega-9 fatty acid), eicosenoic acid (a monounsaturated omega-9 fatty acid), erucic acid (a monounsaturated omega-9 fatty acid), arachidonic acid (a polyunsaturated omega-6 fatty acid), eicosenoic acid (an omega-6 fatty acid, 11,14,17-Eicosatrienoic acid), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), linoleic acid (a polyunsaturated omega-6 fatty acid), linoleidic acid (an omega-6 trans fatty acid), or α-linolenic acid (ALA).

[0033] In one embodiment, in formula 1, R is -O-R4-OH (R4 is -(CH2)n-, where n is an integer from 1 to 10), and more specifically, it can be -O-C2H4-O-C2H4-OH, -O-C3H6-O-C3H6-OH or -O-C2H4-O-C4H8-OH.

[0034] In one embodiment, R is a polyurethane-derived substituent, (R4 and R5 are each -(CH2)n- (n is an integer from 1 to 10), and one of the terminal -OH groups becomes a connecting moiety.)

[0035] In one embodiment, R is a PET-derived substituent, (One of the -OH groups at the end becomes a linking moiety.)

[0036] In one embodiment, R1 in the above formula 1 may be -C3H6-, -C2H2-, -C4H8-, -C2H4-O-C2H4-, -C3H6-O-C3H6- or -CH2-CH(OH)-CH2-.

[0037] According to one embodiment, the A substituent may be an alkyl group having 1 to 10 carbon atoms, -(CH2)n-OH, or -(CH2)n-CH(OH)-(CH2)n-OH (wherein n is an integer from 1 to 10).

[0038] In one embodiment, the A-1 substituent can be -(CH2)nO-R6, -(CH2)nO-(CH2)nO-R6, -(CH2)nO-(CH2)n-OH, or -(CH2)nO-(CH2)nO-(CH2)n-OH (wherein n is an integer from 1 to 10, and R6 is an alkyl having from 1 to 10 carbon atoms).

[0039] According to one embodiment, the compound of formula 1 may be selected from the following formulae 1-1 to 1-12:

[0040] [Chemical Formula 1-1]

[0041]

[0042] [Chemical Formula 1-2]

[0043]

[0044] [Chemical Formula 1-3]

[0045]

[0046] [Chemical Formula 1-4]

[0047]

[0048] [Chemical Formula 1-5]

[0049]

[0050] [Chemical Formula 1-6]

[0051]

[0052] [Chemical Formula 1-7]

[0053]

[0054] [Chemical Formula 1-8]

[0055]

[0056] [Chemical Formula 1-9]

[0057]

[0058] [Chemical Formula 1-10]

[0059]

[0060] [Chemical Formula 1-11]

[0061]

[0062] [Chemical Formula 1-12]

[0063]

[0064] (R and R1 are as defined in the above chemical formula 1.)

[0065] According to one embodiment, the molecular weight (g / mol) of the polyol compound represented by the above chemical formula 1 may be 2,000 or less; 1,900 or less; 1,800 or less; 1,600 or less; 1,400 or less; 1,200 or less; 1,000 or less; 800 or less; or 100 or more; 300 or more; 400 or more; 700 or more; 900 or more; 1,100 or more; or 1,500 or more.

[0066] According to one embodiment, the carbon 14 isotope ratio of the polyol compound represented by the above chemical formula 1 may be 50 to 99.

[0067] According to one embodiment, the light transmittance of the polyol compound represented by the above chemical formula 1 may be 50% or more; 60% or more; 70% or more; 80% or more; or 90% or more. The light transmittance may be related to a wavelength of 400 nm to 600 nm.

[0068] According to one embodiment, the viscosity (CP (mPa·s), 20°C) of the polyol compound may be 50 to 1000.

[0069] According to one embodiment, the present invention can provide a composition comprising a polyol-based compound represented by the chemical formula 1 of the present invention.

[0070] According to one embodiment, the composition may be a precursor or raw material composition for polymer synthesis, a composition for various molding processes, etc. For example, the composition may be a polyurethane precursor composition, which may form a polyol-based segment among the segments of polyurethane.

[0071] According to one embodiment, the polyurethane precursor composition may include a diol compound, a polyol compound, a polyisocyanate, etc. The content, composition ratio, components, etc. may be set depending on the composition of the polyurethane segment, functional group, molecular weight, chain extender, etc., and are not specifically mentioned in this document.

[0072] According to one embodiment, in addition to the polyol compound represented by the above chemical formula 1, it may further include polyether polyol, polycarbonate polyol, and polyester polyol; and compounds introducing ionic functional groups.

[0073] In one embodiment, the polyisocyanate compound may be an aromatic polyisocyanate, an aliphatic polyisocyanate, an alicyclic polyisocyanate, and the like. For example, the polyisocyanate compound may be, but is not limited to, 1,3-phenylenediisocyanate, 1,4-phenylenediisocyanate, 2,4-tolylenediisocyanate (TDI), 2,6-tolylenediisocyanate, 4,4'-diphenylmethanediisocyanate (MDI), ethylenediisocyanate, tetramethylenediisocyanate, isophoronediisocyanate (IPDI), 4,4'-dicyclohexylmethanediisocyanate (hydrogenated MDI), cyclohexylenediisocyanate, and the like.

[0074] According to one embodiment, the ionic functional group introducing compound may be a compound containing an anionic functional group including a carboxyl group, a sulfonic acid group, a phosphoric acid group, etc. Examples thereof include, but are not limited to, dimethylolpropionic acid, dimethylolbutanoic acid, dimethylollactic acid, etc.

[0075] According to one embodiment, the composition may be in the form of a solid (e.g., powder, crystal, film, bead, plastic, etc.), a semi-solid (e.g., gel), an emulsion, a suspension, a liquid, etc.

[0076] According to one embodiment, the polyol compound represented by the above chemical formula 1 may be present in the composition in an amount of 1 wt% to 100 wt%, 1 wt% to 99 wt%, 1 wt% to 90 wt%, or 10 wt% to 60 wt%, or 10 wt% to 40 wt%.

[0077] According to one embodiment, the polyol compound represented by the above chemical formula 1 may be reacted in the presence of a reaction raw material and a catalyst at a temperature of room temperature to 300°C; room temperature to 280°C; room temperature to 250°C; room temperature to 200°C; room temperature to 180°C; room temperature to 150°C; 50°C to 100°C; or 70°C to 90°C for 30 minutes or more; 1 hour or more; 5 hours or more; 10 hours or more; 15 hours or more; or 20 hours or more. The above-mentioned time may be appropriately selected in consideration of the reaction completion time. After completion of the reaction, the desired product may be obtained using a process known in the technical field of the present invention, such as cooling, separation (filtration, extraction, etc.), washing, recrystallization, chromatography, drying, etc., which is not specifically mentioned in this document.

[0078] According to one embodiment, the structure of the target product can be determined using analytical methods known in the art of the present invention, such as IR, NMR, XRD, XPS, molecular weight (GPC, MASS, etc.), which are not specifically mentioned in this document.

[0079] Example

[0080] A polyol was synthesized by reacting soybean oil and DEG with an alkaline catalyst at temperatures ranging from room temperature to 300°C for more than 5 hours. The molar ratio of soybean oil to DEG was approximately 1:1. The structure of the synthesized product was confirmed by measuring the following.

[0081]

[0082] (R1 is -C2H4-O-C2H4-OH, R corresponds to the hydrocarbon chain of fatty acid (RC(O)-OH) contained in soybean oil.)

[0083] Hydroxyl value measurement (KS M065), molecular weight measurement (GPC), biocarbon content measurement (ASTM D 6866-22), NMR, IR, viscosity, optical transmittance, carbon isotope, and viscosity were measured. The structure of the synthesized product was confirmed, and the related physical properties were confirmed to be within the range described in this document.

[0084] Although the embodiments described above have been described in terms of limited embodiments, those skilled in the art will appreciate that various modifications and variations can be made based on the above teachings. For example, appropriate results can still be achieved if the described techniques are performed in a different order than described, and / or the described components are combined or combined in a different manner than described, or are replaced or substituted with other components or equivalents. Therefore, other implementations, other embodiments, and equivalents of the claims also fall within the scope of the claims described below.

Claims

1. A polyol compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, R is a substituent derived from an alkane or alkene or a fatty acid or fatty acid ester having a hydrocarbon group of 4 to 28 carbon atoms, or R is, R3-NH- (R3 is a polyurethane-derived substituent, containing one or more moieties and -OH groups), or (R4 is a substituent derived from polyethylene terephthalate, moiety and one or more -OH groups.) R1 is -(CH2)n-, -(CH2)nO-(CH2)n- or -(CH2)n-CH(OH)-(CH2)n- (n is an integer from 1 to 10), R2 may be selected from hydrogen, a monoglyceride-derived substituent, a diglyceride-derived substituent, a triglyceride-derived substituent, an A substituent having 1 to 10 carbon atoms and composed of hydrogen and oxygen, or an A-1 substituent having 1 to 10 carbon atoms, composed of hydrogen and oxygen, and including at least one ether bond (-OC-) in the molecule (provided that the A substituent and the A-1 substituent do not include an "-OH" group).

2. In paragraph 1, The above R is -O-C2H4-O-C2H4-OH, -O-C3H6-O-C3H6-OH, -O-C2H4-O-C4H8-OH (R4 and R5 are each -(CH2)n- (n is an integer from 1 to 10) or A polyol compound.

3. In paragraph 1, A polyol compound, wherein the above A substituent is an alkyl group having 1 to 10 carbon atoms, -(CH2)n-OH, or -(CH2)n-CH(OH)-(CH2)n-OH (where n is an integer from 1 to 10).

4. In paragraph 1, A polyol compound, wherein the above A-1 substituent is -(CH2)nO-R6, -(CH2)nO-(CH2)nO-R6, -(CH2)nO-(CH2)n-OH, or -(CH2)nO-(CH2)nO-(CH2)n-OH (wherein n is an integer from 1 to 10, and R6 is an alkyl having 1 to 10 carbon atoms).

5. In paragraph 1, The above polyol compound is a polyol compound selected from the following chemical formulas 1-1 to 1-12: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] 6. In paragraph 1, A polyol compound represented by the above chemical formula 1, wherein the molecular weight (g / mol) of the polyol compound is 2,000 or less.

7. In paragraph 1, A polyol compound represented by the above chemical formula 1, wherein the carbon 14 isotope ratio of the polyol compound is 50 to 99.

8. In paragraph 1, A polyol compound having a light transmittance of 50% or more.

9. In paragraph 1, A polyol compound having a viscosity (CP, 20°C) of 50 to 1000.

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